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Taxes, Estate Planning and Financial Theory:

1.
Taxes, Estate Planning and Financial Theory:
New Insights and Perspectives
By
Robert M. Dammon,*
Chester S. Spatt*
and
Harold H. Zhang**
Revised March 15, 2004
*Carnegie Mellon University
**University of North Carolina
We gratefully acknowledge financial support from the Institute for Quantitative Research
in Finance (the Q-Group) and the Teachers Insurance Annuity Association—College
Retirement Equity Fund.
1

2.
Taxes, Estate Planning and Financial Theory: New Insights and Perspectives
Abstract
We examine how financial theory and economic principles offer guidance and
predictions about the organization of investments and asset allocation decisions given the
structure of taxes in estate--planning situations. We provide insight about many of the
conventional approaches to estate planning and suggest how these strategies can be
enhanced. For example, we show that the advantage of the reset provision by which the
investor’s capital gains tax bases are adjusted to the market value at the time of death is
greater in the presence of individual rather than joint ownership of assets, provided that at
the first death of one of the joint owners the basis is reset to an average of the date of
death value and the survivor’s original cost. We analyze asset location and distribution
policies in the context of trusts that are outside of the taxable estate of its principal
beneficiary as well as direct funds owned by the beneficiary, highlighting the interaction
between estate taxation and the reset of the capital gains tax basis at death. We compare
the optimal decisions for traditional tax-deferred accounts and after-tax (“Roth”) IRAs.
Finally, we also examine the value and importance of borrowing in various contexts in
estate planning.
2

3.
Taxes, Estate Planning and Financial Theory: New Insights and Perspectives
1. Introduction
In this paper we examine how financial theory and economic principles offer guidance
and predictions about the organization of investments and asset allocation decisions given
the structure of taxes in estate--planning situations. We provide insight about many of the
conventional approaches to estate planning and suggest how these strategies can be
enhanced. The standard approaches to estate planning include the use of (a) a “credit
shelter” trust and individual asset ownership titles to allow both spouses to utilize their
full lifetime estate and gift tax exemptions, (b) the use of a partnership vehicle in order to
obtain a valuation discount, (c) irrevocable life insurance trusts to exclude life insurance
policies from the taxable estate, (d) lifetime gifting to reduce the taxable estate and (e)
generation—skipping trusts to limit the taxation of estates across generations. These are
some of the principal tools recommended by attorneys, as a function of the size of the
investor’s estate and other family--specific circumstances.
While the institutional arrangements examined are ones widely used in practice, the
theoretical lens we use provides novel insights for understanding estate--planning
problems and issues. 1 For example, we show that the advantage of the reset provision by
which the investor’s capital gains tax bases are adjusted to the market value at the time of
death is greater in the presence of individual rather than joint ownership of assets,
provided that at the first death of one of the owners the basis is reset to an average of the
1
We assume throughout our analysis that the investor’s marginal beneficiaries are individuals (e.g., family
members) rather than charitable organizations as the planning issues and opportunities would be
substantially different in the latter context.
3

4.
date of death value and the survivor’s original cost. The option value that results is
greater in the individual ownership scenario than in the case of joint ownership because
of greater flexibility in the diversification opportunities after the reset at death due to
greater spreading of the survivor’s overall tax bases (which are the exercise prices of the
investor’s tax-trading options). This exploits within a portfolio—theoretic context the
option-theoretic notions that a portfolio of options is more valuable than a single option
on the composite portfolio and that option values are convex in the exercise price (see,
e.g., Merton [1973]). While the treatment of the basis assumed is appropriate in non-
community property states (41 of 50 states within the United States), in the community
property states the entire basis of “community property” assets is reset to the market
value at the death of either owner as the full position is presumed 100% owned by each
of the two marital owners. 2 Consequently, the value of the reset provision and the
resulting incentive of the elderly to own equity are particularly large for “community
property.” However, the reset provision does not affect the titling of “community
property” because the 100% reset obtains whether the asset was titled to the deceased, the
survivor or jointly owned.
We also analyze asset location and distribution/contribution policies in the context of
trusts that are outside of the taxable estate of its principal beneficiary as well as direct
funds owned by the beneficiary. We identify optimal policies for investors with separate
funds that are inside and outside the investor’s taxable estate (such as the inherited funds
in a “credit shelter” trust), where the funds inside the taxable estate allow reset of the tax
2
The community property states are Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas,
Washington, and Wisconsin.
4

5.
basis at death (making equity more attractive, especially for the elderly) and the funds
outside the taxable estate do not benefit from the capital gains reset. Consequently, for a
sufficiently small value of wealth owned by a couple, it would be optimal to not establish
a credit shelter trust (even if costless to do so) or alternatively, place only a limited
amount of funds within it (because the likelihood of estate taxes at the second death is
sufficiently small) and instead benefit from the reset of the capital gains bases on those
assets at the second death. For investors with moderate wealth levels the value of the
credit shelter trust can be less than the potential value of the reset of the tax bases at
death. Our approach suggests that the amount of funding of the credit shelter trust should
equate the marginal expected estate tax savings and marginal benefit from the reset
provision at the second death under the risk-neutral measure at each point in time that
there is a marginal funding or distribution decision between the accounts (e.g., the
optimal funding or distribution choice is not at a corner). In the face of a rising estate tax
exemption threshold over time, investors will find it less attractive over time to utilize the
credit shelter provision in order to more fully utilize the basis reset at the second death. 3
Our analysis of the initial contribution and periodic distribution decisions is one of
several ways in which we examine the interaction between estate and income taxes.
Our analysis addresses the reset provision at death and asset titling such as joint vs.
individual ownership (Section 2), “credit shelter” trusts (Section 3), several insights about
the value of tax-deferred investing in both traditional tax-deferred programs and Roth
IRAs (Section 4), and the value and importance of borrowing in various contexts in estate
3
However, starting in 2010 the amount of capital gains that can be reset at death will be somewhat limited.
5

6.
planning (Section 5). The paper concludes (Section 6) with a brief discussion of some
numerical solutions that we will undertake to complement and complete this analysis.
2. The “Reset” Provision and Asset Titling
One of the most important decisions confronting an investor in estate planning is the
ownership form and titling of various assets. In this section we examine how the reset
provision at death, through which the investor’s tax basis is reset to the market value,
influences efficient titling of assets by a marital couple. 4 This analysis uses option--
pricing principles to reach conclusions that go substantially beyond the conventional
advice of attorneys and estate planners concerning asset titling. This points to an
important advantage of individual titling in many circumstances that increases with the
value of the investor’s assets and is robust to situations in which the individuals’ estate
tax exemptions have been fully exploited.
The traditional advice of attorneys has emphasized the importance of titling of some
assets in the names of the individuals in a marital couple (rather than joint titling of those
assets) for estate tax purposes in order that the assets pass through the owner’s WILL to
be available to fund a “credit shelter trust” created under that WILL rather than passing
directly to the joint owner. This strategy allows a marital couple to utilize the exemption
from estate taxes ($1,500,000 per person in the United States starting on January 1, 2004)
4
The potential value and impact of the reset provision at death was first highlighted in finance by the
analysis of Dammon, Spatt and Zhang (2001a) in which the investor’s exposure to risky securities increases
with age as a consequence of the increasing value of the reset provision and the efficient tradeoff between
realizing capital gains and portfolio rebalancing. The basic notion of tax-timing options and their
importance to financial asset valuation was developed by Constantinides (1983, 1984) and extended by
Dammon and Spatt (1996).
6

7.
on each of the partner’s deaths rather than just the second death (the initial exemption
would be lost if all of a married individual’s assets were passed directly to a spouse at
death). Individual rather than joint ownership (whereby the assets would be automatically
transferred to the survivor after the first death) also allows more flexibility for such “post-
death” options as (a) selecting assets for funding the “credit shelter trust” (which is an
“asset location” issue looking forward), (b) exercising the potential beneficiary’s option
to “disclaim” some or all of his inheritance in favor of the next designated beneficiary
and (c) funding the trust above the exemption amount by prepaying federal estate taxes.
Though these benefits of individual titling beyond the federal estate exemption amount
are small in some circumstances and less emphasized by estate planners than the funding
of the basic “credit shelter” amount, individual titling beyond the federal estate threshold
offers a number of advantages with respect to “post-death” estate planning decisions
(options), in addition to the “reset” treatment highlighted in the text.
Our focus in this section is upon the consequences of asset titling for capital gains rather
than estate taxation. First, we observe that joint titling of assets (by which those assets
directly pass to the surviving owner) is dominated from the perspective of the reset
provision and the subsequent tax-trading opportunities by splitting the assets between the
two individuals (and for example, passing the individual assets at death to the marital
partner by either contractual instructions in the asset titling or by the individual’s WILL),
provided that in the case of a jointly--titled asset, its basis is adjusted subsequent at the
death of the owner dying first to a “blended basis” that reflects the average of the original
acquisition cost (the surviving owner’s previous basis) and the date of death value. This
7

8.
blended basis reflects the blended ownership situation corresponding to joint titling that
prevailed prior to the death and the lack of reset directly available on the one- half of the
position previously owned by the individual who survived. This leads to the same
average basis at the death of one of the owners as the situation in which the assets were
individually and equally owned by one of the two partners, because half of the assets are
reset to the current market value due to the death of their current owner. However, the
joint ownership/blended basis situation does not provide as much option value to the
owner. The surviving owner would be better off retaining a low basis on half of his
shares and obtaining the current market value as his basis on the other half of the shares
(so there are distinct bases for the two groups of shares), because this would facilitate the
ability of the owner to lighten his exposure to the asset with no (or lower) capital gains
tax cost. If the investor sold Q shares he could incur lower tax liability in the individual
titling case, as long as Q was below the full combined position. In fact, if the surviving
owner sold no more than half the overall position, he would incur no immediate capital
gains taxes in the individual titling case, unlike the joint ownership--blended adjustment
case. This is an extension of the idea in option pricing theory (e.g., Merton (1973) in
general contexts and Dammon, Spatt and Zhang (2001b) in the context of tax timing) that
a portfolio of options with different exercise prices is at least as valuable as an option on
the underlying portfolio with the composite exercise price (i.e., convexity of the option
value in the exercise price). Of course, in the situation analyzed here the option
comparison involves ownership by investors whose interests are assumed aligned (the
deceased individual and the survivor) rather than a single owner.
8

9.
From an estate--planning perspective the management of the reset provision is very
important and has significant revenue consequences. The foregone federal capital gains
tax revenue from the reset provision (relative to a system in which capital gains taxes are
paid at death on the unrealized appreciation) exceeds the total revenue from federal estate
taxes [documented in detail by Poterba and Weisbenner (2001)]. This occurs even though
the long-term capital gains tax rate (currently 15% and previously 20% for most
taxpayers with investible assets) is substantially below the federal estate tax bracket (at
least 37%, when positive), due to the relatively large number of taxpayers whose estates
are below the federal exemption amount that benefit substantially from the reset of the
capital gains tax basis at death. 5
Investors desire to minimize their effective overall tax liability (both explicit and implicit
taxes), including both estate and capital gains taxes. In some instances these taxes are
traded off with respect to investor decisions. For example, the estate of a deceased
taxpayer is allowed to use an “alternative valuation date” of six months after the date of
death (instead of using date of death valuations) for all the assets provided the estate is
sufficiently big to owe some federal estate tax. However, if the taxpayer elects the
alternative valuation date it must apply to both estate and capital gains taxes. (Weinstock
(1995) also indicates that it must reduce the estate tax so that the alternative valuation
date concept would not apply if there were no estate tax due based upon the date of death
valuation.) While low valuations are desirable from the perspective of estate taxes, high
valuations minimize the potential capital gains tax liability.
5
This is another form of the observation that only a small fraction of estates pay federal estate taxes.
9

10.
While we have demonstrated that individual titling dominates joint ownership in
circumstances in which the basis is adjusted to the blended basis, equal splitting of the
assets will not in general be the efficient way for a couple to optimize the benefits of the
reset provision. Of course, one situation in which equal division of each security position
would be the efficient manner to optimize the tax-trading options created by the reset
provision would be the situation in which the two partners had identical mortality
likelihoods. From a risk aversion/portfolio diversification perspective there are
diminishing returns to additional sales (or ownership) of the assets, which ensures that
equal division of each asset and basis is efficient when the two partners have identical
mortality likelihood and the objective function treats the partners symmetrically. Much of
the benefit of reducing exposure to an overexposed position can be obtained by scaling
back the position by up to 50%, the amount that can be scaled back without any capital
gains tax cost at the first death in the equal division case with individual titling.
Of course, in most situations the couple possesses some information about their relative
mortality likelihoods as a byproduct of their respective genders and ages, even absent
person--specific health concerns that evolve stochastically. The relevance of mortality
information can be seen by reference to the analysis in Dammon, Spatt and Zhang
(2001a) of the impact upon a single investor of the reset provision in a setting with a
single risky asset and a risk- free security. In this setting an increase in the investor’s
mortality risk profile over time or an increase in the investor’s mortality risk at a given
age will typically lead to greater retention and purchase of the risky security due to the
reduced value of immediate diversification and the potential opportunity at death to
10

11.
adjust the tax basis to the market value. Similarly, if the couple has flexibility to
reallocate their exposure between the individuals constituting the marital couple, then the
high mortality risk investor will tend to hold relatively more of the risky position with
relatively larger gains. This is illustrated by the situation in which one of the individuals
has a relatively limited life expectancy, so that the couple would be oriented towards
allocating exposures with substantial capital gains to the individual in poor health. 6 This
discussion suggests the optimality of skewing the assets held by a couple to reflect their
health circumstances and efficiently exploiting the reset provision. Of course, there often
is considerable uncertainty about which of the marital partners is likely to die first, which
will influence the optimal form of the division of assets, and limit the degree to which
positions should be skewed in the optimal solution from a tax planning perspective. As
noted previously, with a complete lack of information about relative mortalities (or
identical mortality rates) the nature of the diversification benefits implies that equal
splitting is optimal.
The analysis in the earlier portion of this section was based upon the assumption that the
basis of jointly—titled assets would be reset at the first death of the joint owners to a
blended basis equal to the average of the market value at that death and the initial
acquisition cost (i.e., the average of the adjusted basis of the deceased owner and the
survivor). In fact, when the owners live in a community property state (or the asset was
acquired prior to 1977) the basis is fully reset to the current market value at the first
6
We should note that the Internal Revenue Service (IRS) can adjust the bases of marital transfers within one
year of death and can include in the deceased’s estate taxable transfers that occur in the three years
immediately prior to the individual’s death (see Weinstock [1995]). While this influences the specific
tradeoffs confronting a couple with respect to the allocation of its assets, the conceptual point being made
still remains.
11

12.
death. 7 The full reset occurs whenever the asset is “community property,” whether titled
to the deceased, the survivor or jointly owned. Consequently, the reset provision at death
does not affect optimal titling of community property. All marital property in a
“community property” state is treated as “community property,” except for “separate
property” that has not been commingled. 8 When the investor owns or retains “community
property” his incentive to invest in or retain equity is relatively stronger than for
individual ownership in non-community property situations due to the reset at death
being fully triggered by either of two separate deaths. 9 If an individual owns both
“community” and “separate” property (see footnote 8), then the individual would skew
his risky holdings to the “community” property, if it were not costly to do so.
3. The “Credit Shelter” Trust
One of the basic and most widely used estate--planning tools is the “credit shelter” trust
in which individuals set aside assets in a trust (that will remain outside their spouse’s
estate) rather than directly bequeathing them to their spouse (note that there is an
unlimited exemption for transfers to a spouse) in order to more fully utilize the combined
estate tax exemption for both individuals to transfer assets to subsequent generations (if
all of the assets were gifted or bequeathed directly to the spouse, then the estate tax
exemption available at the first death would not be utilized to ultimately transfer assets to
7
We thank Eleanor Blayney and Bart Francis for identifying to us situations in which the basis of jointly--
held property is reset to the full market value at the initial death.
8
“Separate property” can arise due to inheritances or property owned prior to the marriage.
9
We can utilize the setting in Dammon, Spatt and Zhang (2001a) to compare the effect of “community
property” treatment upon the equity allocation assuming complete reset of the bases of all of a couple’s
taxable assets when the first spouse dies (compared to the situation with a single life examined in Dammon,
Spatt and Zhang (2001a)). Then the relevant mortality curve would be that characterizing the first death in
a couple. The resulting increase in the probability of the reset of the tax bases at a point in time implies that
the demand for equity would be higher in community property contexts.
12

13.
the next generation). Typically, the surviving spouse becomes the “income beneficiary”
of the trust and the children of the couple ultimately receive the “principal.” This
structure can arise in various ways including through a revocable trust created during the
grantor’s lifetime or under the terms of the grantor’s WILL (and not funded until death).
While lawyers often recommend the use of these trusts (it is perhaps the most basic
estate--planning tool), financial theory provides considerable (and previously
unanalyzed) guidance about the optimal investment and distribution policies for these
trusts.
Typically, the surviving spouse would own funds directly in addition to his role as a
beneficiary of the credit shelter trust. For simplicity, we will assume that the surviving
spouse is making the decisions for the trust. 10 This raises the question of how does the
efficient investment policy for the trust and the individual compare? Alternatively, how
should exposures be located efficiently between the investor’s taxable account and the
credit shelter trust? In a somewhat related context, Dammon, Spatt and Zhang (2004) and
Huang (2000) examine the efficient asset location policy for an investor investing taxable
and tax-deferred funds. We will abstract from the presence of a tax-deferred account to
highlight the portfolio differences between the personal (taxable) account and the credit
shelter trust. We also assume throughout our discussion that the investor’s beneficiaries
and those of the credit shelter trust coincide to avoid differences in preferences distorting
the location or distribution decisions and rely upon arbitrage reasoning to reach our
conclusions.
10
The surviving spouse is often a trustee of the credit shelter trust, though should not be the only trustee so
that the assets are considered outside the survivor’s “complete control” and taxable estate.
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14.
To examine the differences in optimal investment (and distribution) policies it is useful to
identify the major differences in tax treatment between the taxable personal account and
the trust. Three of the main differences are that (a) the assets in the credit shelter trust
have already received the benefit of the reset of the bases on the component assets at the
first death and are not eligible for additional reset in the trust form, 11 (b) the credit shelter
trust is potentially outside of the taxable estate of the surviving spouse and therefore not
subject to estate taxes at the death of the surviving spouse and (c) the marginal income
tax rates for investment returns earned by the trust and the personal taxable account can
differ (the stated income tax schedule for the trust reaches the maximum tax rate of 35%
at an income level of about $9,200). We examine the implications of these differences
for the trust’s optimal decisions.
The differences in tax environment for the credit shelter trust and the personal taxable
account are important for understanding the optimal location of risks between these
capacities. Under the assumption that the investor’s personal account will ultimately be
subject to estate taxes (at the margin), unlike the credit shelter trust, this suggests that the
investor regards the government as owning a portion of the personal account to reflect
these estate taxes. 12 This suggests a rescaling (re-weighting) of the relative importance of
the accounts (from the investor’s perspective the credit shelter trust is relatively more
11
Of course, the reset provision could be utilized again when subsequent principal beneficiaries of the assets
die.
12
This can be extended to situations in which whether the investor will eventually owe estate taxes is
stochastic or even endogenous to the allocation decision within the account subject to estate taxes.
14

15.
important because of the lack of implicit co-ownership by the estate taxing authority). 13
After adjusting the effective exposure for the rescaling, under a constant marginal estate
tax the estate tax difference itself does not suggest systematic differences in the asset
allocation policy between the personal and credit shelter accounts. 14
Another important difference is the lack of opportunity for reset of the capital gains basis
in the credit shelter account, unlike for the personal account of the surviving spouse. As a
result, equity is relatively more attractive to hold in the personal account, especially when
the investor’s life expectancy is limited and the embedded capital gains are relatively
large so that it would be much more valuable for the elderly to defer the realization of
gains in their personal account (to benefit from the potential impending reset of the tax
basis). To the extent that there are income tax rates differences between the investor’s
taxable account and the credit shelter trust account, the higher rate account should hold
relatively more equity and less bonds than the lower rate account. This reflects the
potential deferral of capital gains and the preferential tax rate applied to long-term capital
gains and dividends. If the credit shelter account has a higher tax rate than the personal
account due to the rate schedule facing trusts increasing to the maximum rate at very low
income levels, the rate effect works in the opposite direction from the pure reset effect
described above. These clientele (arbitrage) arguments are in the spirit of the analysis of
the investment holdings in the taxable vs. tax-deferred account in Dammon, Spatt and
13
An analogous issue about relative scaling of the accounts arises in the treatment of tax-deferred wealth
relative to taxable wealth in Dammon, Spatt and Zhang (2004).
14
In our analysis we assume that the estate (and income tax) rates are constants. However, the progressively
of the actual estate tax schedule suggests a potential reason that elderly investors may not find it optimal to
add equity exposure as they age as additional risk increases the investor’s expected estate tax in some
circumstances due to progressivity. Of course, this argument would not apply if the investor’s marginal
estate tax rate would be unaltered by the various asset allocations policies being considered, i.e., if the
marginal estate tax rate were constant.
15

16.
Zhang (2004) and Huang (2000). Of course, the clientele arguments about asset location
in the credit shelter trust and personal account here also can be extended to incorporate
tax-deferred investing.
The optimal distribution policy by the credit shelter trust also can be addressed. Because
the scheduled income tax rates can be higher for the trust than individual investors (as the
trust reaches the maximum tax bracket of 35% at an income level of about $9,200), it is
sometimes believed that it is optimal to pay the income tax at the individual level if the
individual’s marginal tax rate is below that of the trust. However, this ignores the
requirement that the income be distributed to the beneficiary if the tax is to be paid at the
personal level. If the beneficiary faces potential estate taxes at his own death, then an
important cost to consider is the increase in estate taxes that results from the distribution
of the after- income tax payoff to the beneficiary. Given the high federal estate tax rates,
starting at 37% in practice, distribution of the trust’s income would not be optimal for a
beneficiary who would face future estate taxes with sufficiently high likelihood as the
combined income tax and estate tax for the beneficiary would far exceed the income tax
on trust income. 15 Of course, if the income is not distributed from the trust, there is no
corresponding estate tax cost because the trust itself is outside the beneficiary’s taxable
estate. One important implication of this analysis for the institutional design of the credit
shelter trust is that it is important for the trust document to provide the trustees the option
15
In contrast, if the beneficiary knew that his estate would not be subject to any (e.g., federal or state) estate
taxes, then distribution of the trust’s income would be valuable in order to own more assets personally in
order to benefit from the reset of the tax basis at the beneficiary’s own death. Assuming identical ordinary
income tax treatments, the investor’s optimal distribution (or initial contribution) decision reflects the
tradeoff between the anticipated reset benefits vs. the incremental estate taxes at the beneficiary’s future
death. This tradeoff will be influenced by such variables as the size of the beneficiary’s estate and her age.
The issue of distributing trust income also illustrates how repeal of the federal estate tax would alter
optimal tradeoffs in estate planning.
16

17.
not to distribute income to the surviving spouse (and potentially allow the funds to grow
within the trust rather than requiring their distribution). The argument for a flexible
distribution policy is not simply the general observation that flexibility (options) is
valuable in principle, but more specifically the desire to maximize the funds outside the
estate of the surviving spouse if there is a significant likelihood that the surviving spouse
will be subject to federal estate taxation at his own death, i.e., the option to retain funds in
the trust is often in-the- money.
A disadvantage of bequeathing assets to a credit shelter trust is that when the income
beneficiary (surviving spouse) dies there would not be an additional reset of the tax basis
at that juncture. Consequently, the investor’s decision about the extent to which he should
bequeath assets to the credit shelter trust would be determined by the tradeoff between
the anticipated estate and capital gains taxes at the survivor’s death. 16 As a result of the
progressivity of the estate tax schedule, including the initial estate tax exemption,
investors with relatively small estates could elect not to use the credit shelter trust or
allocate only a small proportion of their assets to it (this is in addition to the liquidity
disadvantage of the credit shelter trust for an investor with moderate new worth). For
example, if a couple were sure that its combined estate would be below the estate tax
exemption, then a direct spousal bequest would provide a second reset of the tax bases at
the survivor’s death. A decision to change the titling of individual assets is a low-cost
way (e.g., without redrafting the investor’s WILL) to alter the usage of the credit shelter
trust as a consequence of the tradeoff being made between anticipated capital gains and
16
This is analogous to the tradeoff after the trust is formed between retaining income in the trust or
distributing it directly to the beneficiary.
17

18.
estate taxes as the investor’s net worth changes. By designating the credit shelter trust as
a contingent beneficiary to whom the surviving spouse can “disclaim” some of the
bequest would be an even more direct way to optimize the tradeoff after death. 17 The
nature of the aggregate tradeoff between estate taxes and capital gains taxes is illustrated
by the earlier observation that the revenue from federal estate taxes is less than the
revenue that would be generated by the taxation of capital gains at death. 18
A standard feature of many credit shelter trusts gives the beneficiary the option to
withdraw up to 5% of the principal (or $5,000, if greater) each year (unexercised options
do not cumulate) in addition to the right to withdraw the income as well as principal for
“health, welfare, maintenance and support.” An adverse consequence of the “5% option”
is that 5% of the trust is added to the beneficiary’s estate when he dies if the option had
not been utilized in the final year of the beneficiary’s lifetime (as the “option” was
available at the time of death!). As a result, this option, unlike most options, is not
innocuous and in light of the potential opportunity to borrow from the trust as well as the
right to withdraw the trust’s entire income and its principal for restricted purposes, many
trusts (or the WILLS that create them) would benefit from dropping the provision! Of
course, footnote 15 points to a situation in which greater opportunity to distribute assets
from the trust could be beneficial. However, greater benefit of the reset of the tax basis at
a beneficiary’s death could be obtained by the beneficiary’s borrowing from the trust
without a formal distribution from the trust that would increase the size of the taxable
17
In various estate planning contexts a source of value often arises from a design in which the trustee
possesses flexibility and can substantially delay decisions, providing for a valuable look-back option.
18
Interestingly, in Canada there is no estate tax, but capital gains taxes become due at death. This suggests a
stronger incentive for those with long remaining life expectancies to hold highly appreciated assets rather
than those with modest life expectancies (there is the opposite incentive in the United States).
18

19.
estate. An alternative solution to the estate tax problem created by the “5% option” is to
make the option available only on the last day of the year (as suggested by Weinstock
(1995)). As long as the individual does not die on that day, there is no estate tax cost
under this alternative.
4. Value of Tax-Deferred Investing
Dammon, Spatt and Zhang (2004) present an analysis of the relative value of tax-deferred
vs. taxable wealth and the investment allocation within these accounts. They document
substantial value to tax-deferred as compared to taxable wealth. These values are
functions of the state variables including the split between taxable and tax-deferred
wealth and the investor’s age and associated mortality risks. They were computed under
the assumption that the tax-deferral opportunity terminated at the investor’s death. Under
current IRS withdrawal regulations, the permitted withdrawals extend significantly
beyond the lifetime of the original tax-deferred accountholder for all choices of
beneficiary. 19 This substantially raises the relative value of tax-deferred funds (and
therefore, the incentive to contribute to tax-deferred accounts).
Recently, there also has been considerable attention to “Roth” IRAs in which the income
tax obligation is prepaid. Under the assumption of constant tax rates and the ability to pay
the tax obligation with personal (taxable) funds, the prepayment of the income tax with
personal funds for the “Roth” IRA scales up the effective tax-deferred investment.
19
The impact of the choice of beneficiary upon the required withdrawals is less than under the prior IRS
rules for distributions from tax-deferred accounts, but still can be substantial. For example, by bequesting
retirement funds to children can result in lower required distributions than if an elderly spouse is the
beneficiary. If the elderly spouse has adequate financial resources, it may be advantageous to do so.
19

20.
Among additional advantages of the “Roth” IRA are that withdrawals are not required
during the investor’s lifetime (in contrast, required withdrawals start at age 70.5 for the
traditional tax-deferred accounts), and the 10% penalty on premature withdrawals only
applies to the after-tax value.
There also is an interesting option for investors who convert a traditional IRA into a Roth
IRA, i.e., the investor can re-characterize (reverse) the conversion. In particular, since the
tax liability is computed based upon the conversion value, it can be optimal to reverse the
conversion if the account value has declined substantially prior to October 15th in the next
year. This also suggests that until the re-characterization option expires (or otherwise has
little value) it can be valuable to locate volatile assets (and especially a highly
concentrated portfolio) in a tax-deferred account, unlike the focus of the location analysis
in Dammon, Spatt and Zhang (2004) and Huang (2000) in generic tax-deferred settings. 20
Similarly, eligible participants can recharacterize a newly funded traditional IRA as a
Roth IRA and a Roth IRA as a traditional IRA until October 15th of the year after the
contribution. To maximize the option value it is advantageous to separate these accounts
by their respective expiration dates (for example, managing separate accounts in which
the option to recharacterize expires on October 15th of the current year, October 15th of
the following year, and the option is no longer ava ilable).
5. The Role of Borrowing in Estate Planning
20
The special tax treatment for employer stock held in 401k plans also alters the conventional asset location
advice.
20

21.
Of course, the optimal policy for distributing trust income can depend upon the
beneficiary’s intertemporal consumption preferences. For example, the beneficiary may
desire the funding to support his optimal intertemporal consumption policy when he faces
liquidity constraints. However, to the extent that the beneficiary can borrow from the
credit shelter trust his optimal consumption profile can be achieved (without distribution
of trust income) because the borrowing would not result in any tax liability and could
(eventually) be repaid (e.g., even if by the beneficiary’s estate). Borrowing allows the
beneficiary to utilize the resources of the trust (if needed) without distributing the funds
to his own taxable estate. 21
This discussion of the income distribution policy of the credit shelter trust points to the
broader potential significance of borrowing in estate planning. Borrowing can help
economic agents achieve their optimal consumption and risk-sharing strategy, while
minimizing the tax liabilities that they face. In the “credit shelter” situation borrowing
allows the beneficiary to minimize the estate taxes that his own heirs incur by minimizing
the need to distribute funds from the trust for which he is the beneficiary to his own
taxable estate. Another commonly--used device in estate planning is a limited partnership
to create minority interests and associated valuation discounts (which have the effect of
decreasing the effective estate tax rate and increasing the effective estate tax exemption)
on the relevant assets. 22 The investor using this device typically becomes the general
21
Notice that the optimal borrowing from the trust typically would not correspond to the amount of the
undistributed after-tax income earned by the trust. Also note that the ability of the trust to borrow would
reflect the collateralized value of its financial assets.
22
The limited partnership approach is sometimes recommended, as the “next step” in planning for an estate
that would face estate tax liability despite using a credit shelter trust structure. Poterba and Weisbenner
(2003) discuss differences in effective taxation rates across asset categories.
21

22.
partner, retaining control of the assets. The ability of the general partner to borrow for his
personal account against these assets enhances the value of this traditional estate-
planning tool. 23 It avoids potential liquidity costs to the investor/general partner
associated with the partnership form, even on lifetime gifts to others by the investor. 24
These arguments highlight the advantages of making sure that partnership and credit
shelter documents allow the option of borrowing.
Dammon, Spatt and Zhang (2001a) point out that borrowing by an elderly investor with
substantial holdings of appreciated stock would allow the i vestor to avoid realizing
n
gains in order to consume, as the investor’s tax basis would be “stepped up” to the
current market value at death. In that situation the investor would borrow to consume
after selling his entire risk- free bond position and any risky assets with losses, thereby
avoiding the need to sell highly appreciated securities to consume. Therefore, the ability
to borrow facilitates the investor’s ability to avoid capital gains taxes efficiently.
Similarly, the ability to borrow may allow the investor the opportunity to become better
diversified in his portfolio structure despite the presence of substantial appreciated
positions, while limiting the sale of the appreciated securities and the associated payment
of capital gains taxes. 25
23
The ability to borrow allows the general partner access to the partnership funds for his consumption needs
despite obtaining the benefit of the valuation discount (on both shares that he will bequest at his death as
well as assets that he had previously gifted as partnership shares in his lifetime).
24
The liquidity costs to the limited partners (as well as the general partner) can be mitigated if the
partnership provides them loans as needed (e.g., in the case of the limited partners up to the amount that
would have otherwise been gifted to them outright).
25
Since the benefit of the “step up” in basis arises only for assets titled to individuals (but not trusts), it also
can be beneficial to borrow from a related credit shelter trust to enhance this benefit.
22

23.
Dammon, Spatt and Zhang (2004) observe that borrowing by an investor with a
substantial tax-deferred retirement account can allow the investor to maximize the “tax-
arbitrage” profits available from purchasing bonds in the tax-deferred account. In fact, if
the investor can borrow without frictions then the optimal portfolio composition is for the
investor to own all of his desired equity in the taxable account, leveraging if necessary,
and neutralizing the leverage through bond holdings in the tax-deferred account (see
Dammon, Spatt and Zhang (2004) and Huang (2000)). 26 The ability to borrow (without
substantial frictions) in the taxable account eliminates the role of equity in the tax-
deferred account as well as the liquidity problems created when a substantial portion of
the investor’s wealth is tax deferred. In contrast, when the investor is unable to borrow in
his taxable account, the investor may purchase equity in his tax-deferred account due to
the constraint limiting his ownership of equity in the taxable account (see Figures 1 and 2
in Dammon, Spatt and Zhang ((2004)).
6. Concluding Comments
In revising the paper we plan to use numerical solutions (extending the approach in
Dammon, Spatt and Zhang (2001a)) to examine the relative values of the reset option in
situations in which there is a single investor vs. a married couple using joint ownership,
assuming either 100% reset of the basis at the first death or reset to the blended basis,
averaging the surviving spouse’s cost and the market value at death. These solutions will
allow us to further examine how individual ownership influences the pattern of holdings
and investor welfare relative to joint ownership and how substantial skewness in
26
Notice that the borrowing occurs in the investor’s taxable account. The analysis is not sensitive to the
statutory restriction that bars or greatly restricts borrowing in tax-deferred retirement accounts.
23

24.
mortality risks between the couple influences the location of risk exposures. In the
analysis of the “credit shelter trust” we plan to quantify (as a function of the investor’s
age and other state variables) how the absence of the reset option influences the relative
investment decisions in the credit shelter trust account vs. the individual’s own taxable
account (which includes the reset option) and the welfare benefit associated with the reset
option over the state space. These comparisons require explicit numerical solution over
the entire state space. Because estate planning issues are much more important for elderly
(as compared to younger) investors, it will be natural to focus these solutions upon the
retirement years, avoiding the need for explicit specification of the labor income
generating process. In addition, we plan to quantify how the recent changes in IRS
distribution rules for tax-deferred accounts enhance the value of tax-deferred wealth and
how the value of Roth vs. traditional tax-deferred funds differ due to the lower effective
penalty on withdrawals and lower required withdrawals. It also would be interesting to
compare the predictions of this analysis with respect to asset titling and asset location to
observed investor behavior.
This paper addresses an important step in developing prescriptive models of how investor
should structure their holdings in realistic settings, i.e., examining both traditional and
novel estate planning approaches through the theoretical lens of analyses of
diversification and taxes.
24